


One Job

by AndreaDTX



Series: What's Your Fantasy? [5]
Category: Supernatural
Genre: Anal Sex, Bottom Dean Winchester/Top Sam Winchester, M/M, Orgasm Delay/Denial, Power Play
Language: English
Status: Completed
Published: 2017-12-21
Updated: 2017-12-21
Packaged: 2019-02-18 05:16:29
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,194
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13093179
Author URL: https://archiveofourown.org/users/AndreaDTX/pseuds/AndreaDTX
Summary: After Sam makes Dean’s biggest sexual fantasy come true, Dean wants to return the favor. But Sam makes him really work for it.Lightly connected to Birthday Wish, but meant as a STAND-ALONE





	One Job

Sam frowns, confused, the page of the book he’s reading frozen mid-turn. “It’s way too early for an ‘early birthday present’. I gave _you_ an early present. We’re just as close to my last birthday as the next. Plus, anticipating May's like tempting fate. Something terrible and life- or world-threatening has happened for, like, the last 13 years. You’d do better calling it a late Christmas present.”

Dean rolls his eyes. “Ok. Merry late Christmas.”

“We don’t celebrate Christmas," Sam replied with a quirked eyebrow. "The last time we did, you were scheduled to die… on my birthday.”

Dean holds up his hands in surrender. Trust Sam to analyze it to death. Geek. “Ok. Fine. Well… You deserve something special for… for doing the research on our last case.”

Sam’s eyes narrow and he holds up the book he’s been reading. “I do the research on _all_ of our cases.”

“And you do a damn good job that deserves to be rewarded.”

Sam stares at him for a second before laughing softly. “Why won’t you just admit it?”

“Admit what?”

Flipping his book closed and tossing it on the table, Sam sits back and crosses his arms. “You want to know what I fantasize about.”

“What? No, I don’t.” He absolutely does.

“You totally do. You can’t stand it that I figured out exactly what you imagine when you jerk off _and_ I made it happen in real life and you have no idea what goes through my head when I’m alone.”

 _Yes._ “No.”

Sam shrugs. “Then what does it matter?”

Now it’s Dean’s turn to frown. “Jeez. Can’t a big brother just wanna do something nice for his kid brother once in a while?”

“Wow. Way to make yourself a sainted martyr there.” Sam snorts with laughter. “Pretty much everything we do both mocks and strains the definition of ‘brotherly love.’”

“Whatever.” Dean snaps, unable to reign in his impatience. “Just tell me already.”

“Nope” Sam shakes his head with a slow cat-that-got-the-canary grin. “If you wanna know, you’re going to have to figure it out, just like I did.”

“Seriously?!”

“Yep. Guess you’ll really have to pay attention. You always swear you know everything about me and how I think and what I’d do, so this should be a piece of cake, right?”

_Oh. Dirty pool…_

“Challenge accepted, little brother.”

 

Over the next week, Dean peppers him with random questions and wild guesses:

“Does it involve other people?” He asks as Sam brushes his teeth.

“Nah,” Sam mumbles around his toothbrush. “Not really a fan of sharing.”

“Does it include dressing up in any way?” Dean asks as they eat lunch in the Impala.

“Nope,” Sam says around a bite of his cobb salad. “We’d be completely naked. Or at least you would be. I think I could go either way.”

“Are we role-playing?” He asks as they walk up to the house of the witness they need to interview.

“Not really,” Sam says. He knocks on the door and pulls his cover badge.

“Does it involve sex toys?” He asks not-so-innocently while Sam is making copies at the front desk of the library.

“Yes,” Sam hisses sharply and blushes underneath the middle-aged librarian’s curious stare.

“Would we be in public or somewhere private?” Dean shouts through the bathroom door.

“Public involves other people,” Sam yells back from where he’s sitting on the toilet.

“Would it be you fucking me or me fucking you?” Dean asks _literally_ in the middle of sex.

Sam’s grabs Dean’s thighs, shifts him to get better access, and forcefully slides his cock home. “What do you think?”

Dean grunts, his eyes rolling back in his head, his breath rasping. He doesn’t respond, but Sam figures he’s got his answer.

“You really like being in control. I mean, like, sexually,” Dean says after Sam suggests he wear his red shirt instead of the black one he’d originally picked.

Sam shrugs. “I like seeing how you react when I push your boundaries, especially when you do something you usually wouldn’t just because I asked.”

 

That night he wakes up to find Dean sitting in a chair by his bed, staring at him. Which in hindsight is probably creepy in ways Dean didn’t intend, particularly given that Sam’s already prone to nightmares.

“Wazzamatter?” Sam mumbles, after his initial startle fades.

“You get off really hard whenever I take completely over. You’re basically a fuck toy and I’ve never seen you come harder... Do you want a chance to do that to me?”

Sam remains quiet. For a second, Dean thinks he might’ve gone back to sleep. Then he realizes it’s something more.

“Holy shit.” Dean stands up so fast he nearly tips his chair over, triumphant glee lighting his face, even in the low light of the room. “That’s it. I figured it out!”

“Congrats,” Sam grumbles like he’s not sure how he feels now that this information is in Dean’s hands.

“Dude, don’t be like that. I’m totally in. This is going to be so fucking hot!”

Dean’s enthusiasm is contagious. Sam sits up and rubs at his eyes.

“So what? Are we doing this now?”

“Now? Fuck, no. I’m tired. I’ve been staring at you for hours.”

Sam can’t help his laugh.

Dean smirks back chagrined. “How about tomorrow evening? Or, I guess it’s later today at this point. Let’s say six o’clock on the dot. It becomes your show. Whatever you want.”

“Yeah, okay. Thatsoundsawesome,” Sam says, dropping back into his pillow.

 

Dean spends most of the next day half-hard. By five ‘til six, Dean is quietly loitering outside of Sam’s room trying to pretend he’s not.

“You can come in, you know,” Sam calls through the door. “You decided six on the dot, not me.”

Apparently, he wasn’t as quiet as he thought.

Embarrassed at being caught, Dean opens the door slowly, and walks in as casually as possible, taking in all the details. Sam’s bed is neatly made. There’s a high-backed, wooden arm chair from the library in the center of the room. The overhead is off in favor of softer light from two corner lamps. Dean’s gaze wanders over to Sam’s nightstand, which has been moved next to the chair. A bottle of lube, a pair of handcuffs, a towel, and two identical flashlights—no, _fleshlights_ \- resting in a small, self-heating, see-through tub of water.

“Strip,” Sam orders, pulling Dean’s attention back to him. “Everything. Off.”

Dean doesn’t hesitate, shucking both shirts and jeans, toeing off his shoes and socks. He’s not ashamed to admit to being relieved to see Sam doing the same.

“Hands on the chair, on the seat.”

Dean walks over and bends, placing his palms flat on the chair, anticipation twirling through his stomach. Sam shifts him, kicks his feet a little further than hip width apart. The cool draft of the bunker glides over Dean’s skin, forcing a shiver from him. It’s silent for a moment and Dean startles when he feels a touch to his hole. Sam’s fingers.

“You’re fine,” Sam murmurs. “Nothing we’ve never done before.”

He rubs at Dean’s opening, a simultaneously relaxing and arousing touch. It’s not long before Dean’s pushing back into it, silently begging for more. Sam gives him one finger, pushing it all the way in, pulling out to add a second finger, pressing and scissoring, working him open. Sam pulls out, applies more lube, and returns pushing in with two fingers straight away. When he adds a third, Dean grunts.

“You can do this,” Sam reassures him softly. “You’ve done it before. No big deal.”

Dean shifts and grunts, which eventually turns into groans, as Sam rubs and stretches him. Eventually, the overwhelmed _toomuchtoomuch_ feeling melts into moans for more. He whines when Sam slips his fingers out and pulls him up right, an uncomfortable position with his hole throbbing loose and open. Sam shuffles them so Sam is between Dean and the chair and he takes a seat.

“Climb on,” Sam says, sitting on the edge of the seat.

“Umm… with you inside me, right?” Dean clarifies, embarrassed that he has to ask, but wanting to be sure.

“Facing away, with me inside you,” Sam confirms.

Dean turns and straddles Sam’s legs. He bends at the knees and reaches behind him to grip Sam’s cock. He blushes a little at the show he’s gotta be giving Sam right now, but there’s no way around it. He lines Sam’s cockhead against his hole and bears down, grunting as the tip pops through his ring of muscle. The noise grows as Dean lets gravity and his own weight take over and he slides down Sam’s cock. By the time his butt’s firmly in Sam’s lap, Dean’s heart is racing and his own cock is throbbing.

“Good job,” Sam says between kisses to Dean’s neck. He loops an arm around Dean’s waist and uses it to guide Dean with him as he shifts back on the seat. The arms of the chair make it a tight fit. Dean tries to adjust by pulling his legs together, but Sam’s legs are already occupying that space. The only thing he can think of is to pull his legs up and loop them over the arms of the chair. Which apparently was Sam’s intention all along.

“Good boy,” he murmurs, one big hand squeezing Dean’s cock and balls gently but firmly in reward, pulling a long moan from Dean. When he lets go, he reaches over and grabs the handcuffs. He loops the first bracelet around Dean’s right wrist and snaps it closed. He pulls the arm up and back, looping the cuffs around the top of the chair back, and then pulls Dean’s left arm up and secures it. It effectively restrains Dean to the chair back with his arms wrapped around Sam’s neck.

Dean moans and shudders with how exposed he feels, impaled on Sam’s cock, his arms pinned behind his head, his legs spread wantonly, his cock and balls wide open to touch. The thought alone is unbelievably arousing and makes Dean writhe.

Dean squirms until Sam slaps him on the side of the hip.

“Be still,” he orders.

“Sorry,” Dean whispers and slumps against Sam’s chest and waits.

And waits.

And waits.

They stay there, in that position for what feels like forever. Dean can’t figure out what Sam’s goal is and he can barely keep from grinding down every time he feels Sam’s cock pulse inside of him. But this is Sam’s show and he wants Dean to be still. So he does.

After a while, the anticipation dulls, despite his suggestive position, and his mind wanders, his erection waxing and waning. Mostly, waning. With no direct stimulation, only the periodic shift of Sam inside him keeps him even kinda in the game.

Dean’s half-way in la-la land when Sam startles him by shifting. He watches as Sam reaches over and grabs one of the fleshlights that have been soaking in hot water. He dabs it against the towel and presses it against the crook of his elbow, presumably to check the temperature.

Satisfied, he takes ahold of Dean’s semi-erect penis and poises the opening of the toy about an inch away from the head.

“Your only job is to relax,” he murmurs softly but clearly in Dean’s ear. “No bearing down on me. No tensing your arms and legs. No clenching your fingers or toes. No tightening your stomach, no gritting your teeth. None of it. Just sit here, completely relaxed, and I’ll get you there. Understand?”

Dean can already tell this is going to push him to his limits, but he simply nods. “Yes, Sammy.”

Sam works the fleshlight onto Dean’s cock and Dean hisses, immediately tensing his stomach and clenching around Sam. The heat of the sleeve creates a wet, hot, tight vacuum that rivals any hole Dean’s ever had the pleasure of being inside of and sends blood rushing to his cock so quickly it makes him a little light headed. He bears down and tries to thrust into the toy.

Sam tsks and pulls the sleeve off, drawing an aggrieved whine from Dean.

“You’re breaking the rules, the _only_ rule, already. You’re tense all over and I can feel you clenching,” he says with a push of his hips into Dean.

With that thrust, it hits Dean. Sam’s not inside of him to fuck him. He’s using his dick as a freaky internal dipstick to make sure Dean’s following his rules. Dean can’t help the moan that spills out of his mouth.

“Take a deep breath and relax,” Sam orders. “We’ll start back when you’re ready.”

It takes several long minutes, but finally Dean’s tensionless aside from his coarse breathing. Sam lifts the fleshlight to position it. Dean reflexively tenses at the sight.

“Ahht,” Sam grunts in reprimand.

Dean squeezes his eyes shut, but snaps them back open as soon as he realizes what he’s doing. He focuses hard, literally visualizing each muscle letting go.

When Sam seems satisfied, he pushes the toy down, triggering a whining whimper from Dean. The slow up and down motions feel like the slowest, tightest fuck of his life and the effort of staying completely slack already has Dean panting.

“You’re doing so good. I know it’s gotta be hard with this thing sucking at your cock. I don’t know if I could do it. Fucking into a hot, tight hole is the best part of sex.”

Dean groans out a laugh. “You bastard.”

Sam laughs back and kisses the side of his face. “You’re clenching.”

Dean flops his head back, every bit of his focus on keeping his muscles loose and lax. Sam works the toy over him slowly, the sleeve squeaking slickly with every push, Dean moaning weakly with every pull. The noise is a little embarrassing but without permission to tense or grind or bear down, he needs some outlet for the sensations whipping through him.

Eventually, the tightness stops feeling so overwhelming and the inner sleeve of the toy cools to room temperature. For a brief moment, Dean thinks maybe he can handle this.

Then Sam’s pulls the fleshlight off. It releases Dean’s cock, the tension of vacuum seal breaking with a slick, forceful pop that nearly sends Dean flying out of his skin.

Sam shushes him, pulling Dean against his chest and rubbing a big hand soothingly over his stomach. He sticks the toy back into the water, which clouds a little as the pre-cum Dean’s left in the toy trickles down into the container. Sam picks up the second fleshlight, tamping it against the towel and again testing its temperature against the crook of his elbow. He glances at the bottom before turning a dial a single click. Using a finger, he guides the tip of Dean’s cock into the tubing.

Dean groans as the tube glides down. It’s hot again and somehow tighter. The dial must control the vacuum and Sam’s click increased it. Despite his best efforts, Dean’s hips jerk and he thrusts up once and then twice.

Sam slaps a hand against Dean’s stomach. “Not allowed.”

“I know. I’m sorry. I’m sorry,” Dean whimpers, trying to breath. The constant sucks of ‘calming’ deep breaths are making him woozy, but it’s the only technique he can think of. By the time he’s able to make himself go limp, his head is full-on spinning.

“Good job,” Sam murmurs and starts back with his glacially slow strokes.

“You’re going to let me cum eventually, right?” Dean thinks to ask belatedly.

“Absolutely,” Sam assures him. “And it’s going to blow the top of your head off when you do.”

Dean nods and settles, trying to focus on something else, anything other than the delicious torture gliding over his cock sending nearly painful tendrils of pleasure dancing through his body. But anytime his mind really floats away, he unconsciously starts to clench around Sam or his fingers and toes start to curl or his hips begin to move and his inattention is corrected with a stinging slap to his stomach or the inside of his thighs and more than once with a sharp flick to his balls.

Resigned to staying in the moment, he watches the up and down, so desperate to thrust his muscles are burning. He tries to detach from the sensation, but it threatens to overwhelm him. Which seems to be Sam’s objective. He reaches down to cup Dean’s sac with his free hand, rolling Dean’s balls firmly, squeezing the way Dean has taught him to do during killer blow jobs.

Dean nearly sobs, his body screaming at him to grind down and enjoy the sensation. But he knows it’ll disappear if he does. He opens his mouth and lets a long, harsh grunt color the air as he’s trapped between the dueling sensations of the wet, slick, sucking on his cock and the firm, oh-so-good pressure on his balls. He’s nearly hyperventilating by the time he breaks and thrusts up into the toy.

And as he predicted, the brain-melting rubbing is replaced by a punising flick that makes him hiss and tense even more.

“You have one job,” Sam reminds him.

Dean nods shakily and squeezes his eyes shut. Sam, perhaps feeling a small swell of pity or benevolence or whatever allows it for a brief moment, even stilling the fleshlight. But it’s only a brief reprieve before Sam taps a finger against his eyelids.

“Open and relax.”

Dean does as ordered, albeit with great difficulty, humming loud and off-key as Sam puts the cock sleeve back into motion. The humming works to keep him lax, but his breathing is falling out of control as he watches Sam’s free hand creep up, up, up past his stomach to his chest to trace lazy circles around Dean’s nipples. The fingers trail around and around until Dean loses the teasing challenge and tenses, pulling away from the tickling sensation. Which is met with a long, sharp pinch of his nipple.

“ _Goddamnsonofabitch!”_

Sam holds the pinch a moment longer, pulling the sensitive flesh out and away from Dean’s body, before letting go and licking Dean’s ear, somehow never stopping his movement with the cock toy. “You have one job. Relax.”

Dean shudders. “I’m trying, Sammy.”

What follows is a series of Dean trying to find subtle ways to cheat and Sam catching and punishing him for it. Clenching hole? Slap to the inner thighs. Flexing toes? Flick to the balls. Clenching the fingers that Sam can’t see because they’re behind his head? Dean gets to hold the squeaker toys they sometimes use as non-verbal safety signals and every squeak is treated like a toe flex.

It’s exquisite, ingenious torture.

When Sam pinches at Dean’s nipples again, Dean literally cries uncle.

“That’s not the magic word, Dean. Is there another word you want to use?” Sam asks, checking for Dean’s safe word.

“Nuh,” Dean mumbles.

Sam licks his neck and speeds up his strokes just enough to be perceptible. “Ok. Then stick to your job.”

Sam pinches and pinches and Dean’s nearly gagging on adrenaline as his brains sends messages up and down his spine, trying to find out why his body isn’t responding to such intense stimulation.

Pinch.

Pinch.

Pinch.

When it eventually fails to provoke a broken hum, Sam realizes Dean’s gritting his teeth. Sam takes that away by shoving three fingers in Dean’s mouth which Dean finds equal parts hot and humiliating. He licks at the underside and sucks tightly at the fingers, causing Sam to thrust really hard in to him for the first time in what feels like hours. His body demands more and he groans in disappointment when Sam decides finger-sucking’s not allowed either. The fingers are just like the cock up his ass, in place to make sure he’s following the rules.

“You’re lucky I don’t have more hands,” Sam murmurs, pressing down on Dean’s tongue with the fingers in his mouth. It makes Dean’s mouth water and tickles at his gag reflex, a sensation Dean goes nuts for when he’s going down on Sam. Sam using the fingers to pull Dean’s face so he’s looking directly at Sam and the gleam Dean sees in his eyes says he knows exactly what he’s doing. Dean groans, almost dizzy with the need to fuck.

Sam switches the toys out twice more, making sure the sleeve he’s using is always hot and wet. The vacuum’s been tightened each time and the stroke is now beyond intense, just this side of painful. At this point, Dean’s limp from exhaustion as much as actual will, and not even trying to stay quiet, instead pushing out a continuous grunting moan. The vocalizations are the only thing keeping him grounded. He can feel his long-awaited orgasm, bubbling, building, burning frustratingly out of reach. It’s growing and it’s going to be big. Really big. He can tell and it scares him just a little bit.

He knows that if he could clench or thrust or Sam would speed up, he’d have cum three times over by now, but it’s like Sam wants to pull the orgasm out of him. And Dean’s agreed to let him.  

Sam keeps working the toy, whispering how fucking hot Dean looks spread out like this, how good and tight his ass feels around Sam’s cock, asking how it feels to have his cock in such a hot, wet hole while another cock is shoved balls deep inside of him, reminding Dean how bad he probably wants to thrust, how much he wants to ride the cock inside him, anything so he can cum.

It takes everything Dean has not to tense and he’s nearing his breaking point.

“Fuck. Sam… Sam… Pleasepleaseplease…” he pleads around Sam’s fingers.

“You’re almost there,” Sam whispers. “I can feel it.”

Dean doesn’t even have to ask what he means. His hole is trembling. His finger and toes, which he’s not allowed to move, are tingling. The unbearable coil of pleasure is spiraling through his stomach, his chest, the back of his throat, even across his tongue, welling up to a frightening intensity. He pushes out Sam’s fingers so he can breathe. He’s panting and nearly choking on his own desire.

When it finally hits, he literally screams. Not a manly grunt, but a loud, ragged scream. The orgasm collides into him like a tidal wave and drags him down. His whole body locks, almost painfully, and Sam finally, _finally_ , speeds up his strokes, pushing Dean further, completely overwhelming his nervous system. Damning the rules, Dean clenches and tightens, writhes and thrusts, and it feels like heaven.

By the time the waves break, dark sparkles are curling at the edge of his vision and he can barely breath. He’s sniffling and tears are running out of the corners of his eyes, but he’s too exhausted to even wipe at them. He collapses onto Sam, letting his head lull back as his body jerks through the last few aftershocks. He rouses enough to realize Sam is gripping him tight, thrusting into him, the jerks of Sam’s body signaling his own orgasm. He tries to squeeze his inner muscles, make it as good as possible, but he’s completely tapped and ends up just resting there, head on Sam’s shoulder, staring dazed at the ceiling, as Sam thrusts and shudders and groans, the heat of his release coating the inside of Dean’s body.  

He moans when Sam pulls the vacuum tube off, his cock stretching until it slips free with an audible _pop,_ to fall limply against his thigh. Sam drops the fleshlight back in the water and it turns nearly-opaque white from the amount of cum draining out of the sleeve. If Dean weren’t so wiped, he’d be impressed with himself.

Sam reaches back and thumbs the safety release on Dean’s cuffs, allowing Dean’s arm to slide down. They both sit, boneless, for a long moment before Sam helps Dean shift his legs to the ground. Dean moans again when Sam helps him out of his lap, Sam’s softened cock slipping from his body. When they’re both on their feet, Sam helps him shuffle-limp to the bed, kicking aside the squeaker balls Dean dropped earlier. Dean would usually shake off this kind of help, but they both know his legs are too unsteady to carry him anywhere.

Sam, not doing much better so soon after cumming his brains out, grabs the towel from the nightstand and gives Dean a cursory wipe down and himself an even briefer once over before collapsing on the bed beside Dean.

“How do you even come up with this kinky shit?” Dean mumbles, his face mashed into a pillow. He still hasn’t moved and his brain is floating on an epic cloud of feel good.

Sam shrugs and blushes. “I dunno. It’s mostly just ‘wouldn’t it be hot if…’ and then my brain just kinda runs with.”

Dean eyes flit over, gaze completely serious. “Dude, I totally kinda wanna hump your brain. Later though. Not right now.”

Sam laughs. “Now who’s the kinky one?”


End file.
